Everything about Sulfoxide totally explained
A
sulfoxide is a
chemical compound containing a
sulfinyl functional group attached to two carbon atoms. Sulfoxides can be considered as oxidized
sulfides. (The use of the alternative name
sulphoxide is discouraged by
IUPAC.) An example of a sulfoxide occurring in nature is
alliin.
Nature of the bond
Sulfoxides are generally represented with the structural formula R-S(=O)-R', where R and R' are organic groups. The bond between the
sulfur and
oxygen atoms differs from the conventional double bond between carbon and oxygen in, say, ketones. The S-O interaction has an
electrostatic aspect, resulting in significant
dipolar character, with negative charge centered on oxygen. The bonding is similar to that in tertiary phosphine oxides, R
3P=O.
A
lone pair of electrons resides on the sulfur atom giving it
tetrahedral molecular geometry as for sp³ carbon. When the two organic residues are dissimilar, the sulfur is a
chiral center, for example, methylphenylsulfoxide.
The energy required to invert this
stereocenter is sufficiently high that sulfoxides are optically stable, that is, the rate of
racemization is slow at room temperature. Chiral sulfoxides find application in certain drugs such as
esomeprazole and
Armodafinil, and they're also employed as
chiral auxiliaries. Many chiral sulfoxides are prepared from
asymmetric catalytic oxidation of achiral sulfides with a
transition metal and a chiral ligand.
Reactions
Sulfides are the usual starting materials to sulfoxides by
organic oxidation. For example,
dimethyl sulfide with
oxidation state of -2 is oxidized to
dimethyl sulfoxide with oxidation state 0. Further oxidation converts the compound to
dimethyl sulfone wherein sulfur has the oxidation state +2.
Sulfoxides, such as
DMSO, have basic character, being are excellent
ligands and readily alkylated. Alkyl sulfoxides are susceptible to deprotonation by strong bases, such as
sodium hydride.
Further Information
Get more info on 'Sulfoxide'.
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